Clockwise from top left: former Liverpool owners George Gillett and Tom Hicks, Ken Bates on the balcony at his Monaco home, Blackburn Rovers owners Balaji and Venkatesh Rao from poultry giant Venky’s, and former Portsmouth chairman Vladimir Antonov.
Photograph: PA, David Levene for the Guardian and Getty Images

Francesco Becchetti, Leyton Orient 2014-

In just two and a half seasons as owner, the waste-management magnate has taken Leyton Orient from the verge of the Championship to the brink of relegation from the Football League and possibly even extinction. Since buying the club from Barry Hearn for £4m, the Italian has overseen nine managerial changes and faced repeated claims of interference in team affairs. In December 2015, he earned himself a six-match ban for kicking Orient’s then assistant manager, Andy Hessenthaler, following a win over Portsmouth. Last week, Orient survived a winding-up order at the high court and Becchetti was given until 12 June to either sell the club or pay off its debts. Waltham Forest council are among the creditors, for providing health and safety advice, as is the company that provides match-day stewards and the official club photographer. If Becchetti fails to either pay or sell up, Orient – bottom of League Two and seven points off the last safe spot – risk going into liquidation and out of existence.

Sisu Capital, Coventry City 2007-

Leyton Orient facing the full fury of a spiteful owner scorned

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In December 2007, Coventry – at the time in the Championship – were saved from administration and a points deduction after being taken over by the hedge fund Sisu Capital. “This takeover can only benefit Coventry City Football Club,” said Iain Dowie, the club’s then manager, echoing a mood of local optimism that would prove horribly misguided. After a decade in the hands of Sisu, the 1987 FA Cup winners – who were in the top flight from 1967 to 2001 – face almost certain relegation to League Two, have no stadium agreement at the Ricoh Arena beyond next season, risk seeing their training ground being sold off for housing and are also contemplating the potential loss of their youth academy in June. On the appointment of Mark Robins as their fourth manager of the season earlier this month, supporters’ group the Sky Blue Trust wished him luck. “Sadly, luck is a commodity we think he’ll need,” came the pointed caveat. City are bottom of League One, 14 points from safety.

The Oyston family, Blackpool 1988-

A swashbuckling Premier League side as recently as 2010-11, it seems scarcely credible that Blackpool currently find themselves in League Two. Karl Oyston is the third chairman from his family, who have been owners since 1988, and could scarcely be more unpopular with the Blackpool Supporters’ Trust, whose long list of grievances include his “lack of a strategic plan”, his “lack of ambition to invest in infrastructure or to grow the club”, his “inability to attract or retain good personnel” and his “loaning football club monies out to other Oyston businesses”. The Oystons have not helped endear themselves to Blackpool fans by showing almost total indifference to their protests and either suing or threatening to sue several for libel. Two years ago, supporters around the UK raised the £20,000 needed by the retired pensioner and Blackpool fan Frank Knight, who agreed to pay the sum to avoid going to court over allegations he made about the Oystons on Facebook.

Douglas Craig, York City 1990-2002

The only one of 92 Football League chairmen to refuse to sign up to the Let’s Kick Racism Out of Football charter, Douglas Craig enjoyed considerable early popularity as York City owner as the club won promotion to the third tier of English football and knocked Manchester United out of the 1995-96 League Cup. No fan of on-field frippery, the former Tory councillor was heard ordering Ginner Hall to “cut out the fancy stuff!” after the left-back nutmegged Ryan Giggs at Old Trafford. In 1999, Craig and his fellow directors incurred the wrath of Minstermen fans by transferring ownership of York’s much-loved city-centre home, Bootham Crescent, to a holding company in which he owned a large stake for £165,000, before trying to force the club to buy back their own ground for £4.5m or face extinction. Craig was also instrumental in the FA process that enabled Wimbledon’s owners to relocate their club to Milton Keynes. Within a couple of years of his exit, York were in the Conference and despite escaping once are facing relegation from the National League.

Former York City chairman Douglas Craig, centre, in the Bootham Crescent directors’ box, 2002. Photograph: John Giles/PA Archive/PA Images

Ken Richardson, Doncaster Rovers 1992-1998

In 1999, Ken Richardson was sentenced to four years in prison for conspiracy to commit arson for his part in a plot to burn down Doncaster Rovers’ then ground, Belle Vue. He had hoped to claim on the insurance and force a move to a new stadium that the local council had previously vetoed. His trial heard that in 1995, the chairman had paid a former SAS soldier, Alan Kristiansen, to start the fire. Kristiansen and two accomplices caused £100,000 of damage to the main stand, only to be caught after Kristiansen’s mobile phone was found at the scene. Between the arson attack and his conviction, Richardson oversaw Doncaster’s relegation to the Conference: in 1997‑98 they lost 34 out of 46 matches and went down with a goal difference of -93. At one point they were managed by Mark Weaver, whose previous relevant experience was running the club lottery at Stockport. Rovers’ story since has been somewhat happier: now at the Keepmoat, they have had five seasons in the Championship and despite a slump in recent years they should be promoted from League Two this May.

The Venky family, Blackburn Rovers 2010-

Since purchasing Blackburn Rovers in 2010 for £23m, the Venky family has transformed the club from Premier League staples for more than a decade to Championship strugglers currently flirting with relegation to League One. Upon buying Rovers from the Jack Walker Trust, the Indian poultry magnates took on debts estimated at between £10m and £20m, a figure that had escalated to £104m by last May. Their revolving door managerial appointment policy began with the dismissal of Sam Allardyce in 2010 and the current manager, Tony Mowbray, is their seventh in seven years. Among his predecessors, Henning Berg lasted 57 days while the Norwegian’s successor, Michael Appleton, was in place for the comparatively long haul of 67. Attendances at Ewood Park continue to dwindle as loyal fans tear their hair out at the sight of their best players constantly being sold without being adequately replaced. Meanwhile only silence emanates from the Rovers boardroom.

Tom Hicks and George Gillett Jr, Liverpool 2007-2010

In the proud history of Liverpool Football Club, the brief tenure of the American businessmen Tom Hicks and George Gillett Jr from 2007 to 2010 is a period most fans are happy to consign to the dustbin. It seems unthinkable that such a massive club could have been brought to the brink of administration, but that’s exactly what the American duo managed before a London high court ruling severed their ties with Anfield. Having bought Liverpool with loans, they eventually saddled the club with so much debt that interest payments amounted to around £100,000 per day. They also presented grand plans for a 60,000-seat stadium in Stanley Park that would never be built. Within a year of taking over at Anfield, the working relationship between Hicks and Gillett had broken down and they were eventually sent packing by a high court judge, who labelled them “untrustworthy” before they walked away empty-handed to lick their wounds as control passed to their Bostonian compatriots, Fenway Sports Group.

Ken Bates, Chelsea 1982-2003

Ken Bates's career traced change in football from game to big business

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Following spells at Oldham and Wigan Athletic, Ken Bates owned Chelsea for 21 years before selling the heavily indebted Blues to Roman Abramovich, after they reached the Champions League on the last day of the season. A controversial and outspoken character, Bates alienated fans of the club he had bought for £1 in a number of innovative ways while simultaneously transforming Chelsea from a struggling second-tier side into an established top-flight club. The installation of an electric perimeter fence to deter hooligans around the pitch at Stamford Bridge was a particular highlight, although Bates was forced to take it down again when his wheeze was rejected by the Football Association. He was also sued for libel by one supporter after describing one fans’ group as “parasites” and prompted fury by describing his former vice-chairman Matthew Harding as “evil” a year after his untimely death in a helicopter crash. In 2005 he pitched up at Leeds, where the bickering continued, much of it with his former club and the Russian oligarch who had bought it.

Peter Ridsdale, Leeds United 1997-2003

In his role as chairman of Leeds United, Peter Ridsdale was initially a success, funding a team that reached the 2001 Champions League semi-finals, but his ludicrous overspending prompted the financially banjaxed club’s slide out of the Premier League, through the Championship and into League One. When Ridsdale resigned in March 2003, Leeds were valued at £12m with debts of £79m and details emerged of the often eye-watering sums that had been squandered on compensation payments to sacked managers, exorbitant player wages, private jet hire, a fleet of 70 company cars and tropical fish for Ridsdale’s office. “Fifteen months after I left, Leeds got relegated and suddenly it’s Peter Ridsdale’s fault,” said Ridsdale, who has since been disqualified as a company director but continues to work in football. “It is a myth that we overspent.” Seth Johnson, who is believed to have earned £37,000 per week over four years in which he made 53 appearances, could be excused a wry smile.